Method to produce hyaluronic acid functionalized derivatives...

C - Chemistry – Metallurgy – 08 – B

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C08B 37/08 (2006.01) A61K 47/36 (2006.01) C08J 3/075 (2006.01)

Patent

CA 2744892

In this invention a two steps procedure is described useful to insert functional groups to the hyaluronic acid (HA), through the formation, in organic solvent, of a particular active group on hydroxyl groups of HA and subsequent substitution, on the inserted active group, with a pendant portion containing at least in its terminal portion a nucleophilic functional group, NH2-R. The group inserted by nucleophilic substitution can contain in another its terminal portion a further nucleophilic functional group, in a way to be easily exploitable to further chemical functionalizations, such as an example to obtain the methacrylation of HA functional groups, to obtain photocrosslinkable derivatives. Both direct derivatives of the proposed process and those obtained by the further functionalization can be employed to produce hydrogels.

L'invention concerne un procédé en deux étapes qui permet d'insérer des groupes fonctionnels dans de l'acide hyaluronique (HA), et consiste à: former dans un solvant organique un groupe actif particulier sur des groupes hydroxyle du HA, et substituer ultérieurement, sur le groupe actif inséré, une partie pendante contenant au moins dans sa partie terminale un groupe fonctionnel nucléophile, NH2-R. Le groupe inséré par substitution nucléophile peut contenir dans une autre partie terminale un autre groupe fonctionnel nucléophile, qui peut être facilement exploité afin de former d'autres fonctionnalisations chimiques, pour obtenir par exemple la méthacrylation de groupe fonctionnels de HA en vue de produire des dérivés photoréticulables. Les dérivés directs du procédé de l'invention ainsi que ceux obtenus par une autre fonctionnalisation peuvent être utilisés pour produire des hydrogels.

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